Balance between allylic C-H activation and cyclopropanation in the reactions of donor/acceptor-substituted rhodium carbenoids with trans-alkenes

被引：51

作者：

Davies, Huw M. L. ^{[1
]}

Coleman, Michael G. ^{[1
]}

Ventura, Dominic L. ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 24期

关键词：

D O I：

10.1021/ol702218w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(II)-catalyzed reactions of aryldiazoacetates with (E)-aryl-substituted alkenes generate C-H insertion products and/or cyclopropanes. The product distribution is influenced by the nature of the donor group on the carbenold, the structure of the (E)-aryl-substituted alkenes, and the rhodium catalyst.

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页码：4971 / 4974

页数：4

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共 40 条

[11] Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid [J].

Davies, HML ;

Bruzinski, PR ;

Lake, DH ;

Kong, N ;

Fall, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6897-6907

[12] Highly diastereoselective and enantioselective C-H functionalization of 1,2-dihydronaphthalenes: A combined C-H activation/cope rearrangement followed by a retro-cope rearrangement [J].

Davies, HML ;

Jin, QH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (35) :10862-10863

[13] Double C-H activation strategy for the asymmetric synthesis of C2-Symmetric anilines [J].

Davies, HML ;

Jin, QH .

ORGANIC LETTERS, 2004, 6 (11) :1769-1772

[14] New strategic reactions for organic synthesis:: Catalytic asymmetric C-H activation α to nitrogen as a surrogate for the Mannich reaction [J].

Davies, HML ;

Venkataramani, C ;

Hansen, T ;

Hopper, DW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) :6462-6468

[15] New strategic reactions for organic synthesis:: Catalytic asymmetric C-H activation α to oxygen as a surrogate to the aldol reaction [J].

Davies, HML ;

Beckwith, REJ ;

Antoulinakis, EG ;

Jin, QH .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6126-6132

[16] Intermolecular C-H activation at benzylic positions:: synthesis of (+)-imperanene and (-)-α-conidendrin [J].

Davies, HML ;

Jin, QH .

TETRAHEDRON-ASYMMETRY, 2003, 14 (07) :941-949

[17] Catalytic asymmetric benzylic C-H activation by means of carbenoid-induced C-H insertions [J].

Davies, HML ;

Jin, QH ;

Ren, PD ;

Kovalevsky, AY .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4165-4169

[18] NOVEL-APPROACH TO 7-MEMBERED RINGS BY THE INTRAMOLECULAR TANDEM CYCLOPROPANATION COPE REARRANGEMENT SEQUENCE [J].

DAVIES, HML ;

OLDENBURG, CEM ;

MCAFEE, MJ ;

NORDAHL, JG ;

HENRETTA, JP ;

ROMINES, KR .

TETRAHEDRON LETTERS, 1988, 29 (09) :975-978

[19] Catalytic asymmetric C-H activation of silyl enol ethers as an equivalent of an asymmetric Michael reaction [J].

Davies, HML ;

Ren, PD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) :2070-2071

[20] SYNTHESIS OF HIGHLY FUNCTIONALIZED TROPOLONES BY RHODIUM(II)-CATALYZED REACTIONS OF VINYLDIAZOMETHANES WITH OXYGENATED DIENES [J].

DAVIES, HML ;

CLARK, TJ .

TETRAHEDRON, 1994, 50 (33) :9883-9892

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